Head of Legacy Engineering and Migration Enablement

JOB DESCRIPTION

Head of Legacy Engineering & Migration Enablement

Caava Group · Group Technology · Reports to CTO · Revenue-Critical Portfolio

Reports To

Chief Technology Officer

Key Peers

Evolve Engineering · Platform Operations · Architecture · Data, AI & Workflow Automation · Engineering Operations · Product and Customer Delivery

Direct Reports

Legacy domain/engineering leads, with specialist and delivery capacity as approved.

Portfolio Scope

TurnQuest V4 and associated legacy applications, databases and integrations; customer support, SOWs, technology upgrades and migration enablement.

Role Purpose

Lead Caava’s legacy engineering portfolio, protecting the company’s largest current revenue source while supporting new customer work, necessary modernisation and progressive migration to Evolve.

Balance three priorities: Run, Grow & Modernise, and Migrate. Deliver through domain leads and specialist teams, with clear commitments from peer Heads—not by personally executing every activity.

Core Accountabilities

Protect legacy revenue and customer continuity

• Keep legacy products reliable and customers supported through application support, incident improvement and safe change.

• Maintain engineering coverage and recovery readiness in partnership with Platform Operations.

Build sufficient capacity and a resilient team

• Match commitments to available skills; protect support and migration capacity and prevent double-booking.

• Close capacity gaps through hiring, partners and cross-training.

• Retain critical knowledge, strengthen succession and career paths, and develop teams without weakening customer support.

Deliver customer work and modernisation predictably

• Own engineering delivery of legacy SOWs, projects and lifecycle upgrades, including WebLogic, Java and Oracle.

• Align estimates, resourcing, change control, testing and customer acceptance to meet commitments and protect delivery margin.

• Reduce security, supportability and technical-debt risks through modernisation.

Enable safe, repeatable migration to Evolve

• Own the integrated customer migration plan and legacy-side readiness: business-rule discovery, data conversion, reconciliation and retirement.

• Coordinate peer-owned dependencies, rehearsals, cutover and rollback readiness; build reusable upgrade and migration patterns.

• Retire services, licences and capacity only after customer acceptance, data integrity, operational readiness and commercial exit conditions are met—not against arbitrary dates.

Lead an accountable, commercially sound portfolio

• Own the roadmap, budget, risks and quarterly outcomes across Run, Grow & Modernise, and Migrate.

• Give the CTO and ExCo evidence on delivery, capacity and revenue exposure; escalate trade-offs early with recommendations.

• Challenge or reject unsafe, underfunded or under-resourced commitments.

Weekly Success Measures

Application support and continuity

Critical legacy application incidents resolved within agreed SLAs (%); overdue critical application incidents.

100% resolved within agreed SLAs; 0 overdue critical application incidents.

Capacity and capability

Next 2 weeks’ committed demand covered by named, available capacity, assessed by skill.

100% covered; 0 unapproved double-bookings; minimum support/on-call coverage maintained.

Delivery and modernisation

Due SOW/project and WebLogic/upgrade milestones accepted on time (%);

≥90% completion in each workstream; 0 critical defects at acceptance.

Migration and legacy exit

Due legacy-side migration milestones accepted on time (%); critical reconciliation exceptions at cutover.

≥90% completion; 0 unresolved critical reconciliation exceptions at cutover; all readiness/exit gates met.

Revenue-risk reduction

Revenue-critical incident, lifecycle and resourcing corrective actions completed by their due dates.

100% of actions due completed; 0 overdue revenue-critical actions.

First 90 Daysys 1–30

Understand & Stabilise

Establish a shared baseline of customers, revenue, commitments, capacity and lifecycle risks. Confirm minimum safe coverage and agree the most urgent actions with the CTO.ays 31–60

Agree the Plan

Agree a resourced Run, Grow & Modernise, and Migrate roadmap, including WebLogic upgrades, customer migration waves and peer-owned readiness gates. Put intake controls and priority staffing actions in motion.ays 61–90

Demonstrate Progress

Show control of capacity and forecasts; deliver an agreed milestone and a migration rehearsal or customer proof point with reconciliation. Confirm reusable patterns and present the quarterly portfolio review to the CTO and ExCo.

Experience and Leadership Style

• 5+ years in engineering or enterprise technology, including 2+ years leading teams or complex delivery, support or modernisation portfolios.

• Experience protecting revenue-critical production services while delivering customer SOWs and managing constrained specialist capacity.

• Technical credibility in Oracle, PL/SQL, ADF, WebLogic, Java and integrations, with practical experience in controlled upgrades and data migration.

• Strong commercial judgement across estimation, scope, costs and acceptance; able to communicate evidence, trade-offs and recommendations at executive level.

• Calm, pragmatic and collaborative leadership; transparent about risk, disciplined about commitments and invested in developing people.

• Insurance, financial services or other regulated-industry experience is strongly preferred.

Leadership Approach

• Combine strategic judgement with practical design depth; make timely decisions and maintain standards under delivery pressure.

• Lead calmly, surface risks early, communicate plainly and build teams that deliver without constant escalation.